152547-74-5

Basic information

• Product Name: Carbamic acid, [(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-, 1,1-dimethylethyl ester
• CAS NO: 152547-74-5
• Molecular Formula: C14H21NO3
• Molecular Weight: 251.326
• Mol File: 152547-74-5.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-, 1,1-dimethylethyl ester(152547-74-5)
• EPA Substance Registry System: Carbamic acid, [(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-, 1,1-dimethylethyl ester(152547-74-5)

Safety Data

• Hazardous Substances Data: 152547-74-5(Hazardous Substances Data)

Upstream product

• 138371-45-6 2-N-(tert-butoxycarbonyl)amino-1-phenyl-1-propanone 
• 16735-19-6 2-amino-1-phenylpropan-1-one hydrochloride 
• 19437-20-8 2-(1-oxo-1-phenylpropan-2-yl) isoindoline-1,3-dione 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 93-55-0 1-phenyl-propan-1-one 
• 90-63-1 (RS)-1-hydroxy-1-phenylpropan-2-one 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 
• 1380313-49-4 (4R,5R)-2-(tert-butoxycarbonyl-amino)-1-(benzoyloxy)-1-phenylpropane 
• 1380313-48-3 (4R,5S)-4-methyl-2,2-dioxo-5-phenyl-2γ6-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester 
• 804551-13-1 syn-2-methyl-6-(2-nitro-1-phenyl-propoxy)-tetrahydro-pyran 
• 24424-99-5 di-tert-butyl dicarbonate 
• 705-60-2 1-phenyl-2-nitroprop-1-ene 
• 804551-21-1 [1-methyl-2-(6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 108832-95-7 tert-butyl N-(1-oxo-1-phenylpropan-2-(2R)-yl)carbamate 

Downstream Products

• 37577-07-4 Norpseudoephedrine 
• 76333-53-4 (+)-(2R)-2-Amino-1-phenyl-1-propanone hydrochloride 
• 108832-95-7 tert-butyl N-(1-oxo-1-phenylpropan-2-(2R)-yl)carbamate 
• 77943-39-6 4-methyl-5-phenyloxazolidin-2-one 
• 125133-96-2 (4R,5R)-4-methyl-5-phenyl-1,3-oxazolidin-2-one 

Relevant articles and documents

Asymmetric Transfer Hydrogenation: Dynamic Kinetic Resolution of α-Amino Ketones

A series of α-amino ketones were reduced using asymmetric transfer hydrogenation (ATH) through a dynamic kinetic resolution (DKR). The protecting group was matched to the reducing agent, and following optimization, a series of substrates were investigated, giving products in high diastereoselectivity, over 99% ee in several cases and full conversion. The methodology was applied to the enantioselective synthesis of an MDM2-p53 inhibitor precursor.

Experimental and DEE study of the conversion of ephedrine derivatives into oxazolidinones. Double SN2 mechanism against SN1 mechanism

Sulfonation of the N-Boc derivatives of 1,2-aminoalcohols, such as ephedrine, pseudoephedrine, norephedrine, norpseudoephedrine, thiomicamine, and chloramphenicol yields a mixture of the corresponding oxazolidinones with inversion (erythro derivatives) and!or retention of configuration (threo derivatives)at C5. We suggest a competition between two mechanisms: an intramolecular SN2 process initiated by attack of the carbonyl oxygen of the Boc group to the benzylic carbon and the other one through a double SN2 process. In the erythro derivatives the first mechanism is predominant, while in the threo derivatives both mechanisms have similar energy. This hypothesis is supported by theoretical calculations and additional experimental assays.

The use of phosphinamide N-protecting groups in the diastereoselective reduction of ketones

The phosphinamide N-protecting group is demonstrated to be an effective directing group for the diastereoselective reductions of proximal ketones.